1308298-23-8|(2-(Trifluoromethyl)pyrimidin-5-yl)boronic acid| Ambeed

Structure of 1308298-23-8

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Quality Control of [ 1308298-23-8 ] Purity: 97% SDS Specification

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Product Details of [ 1308298-23-8 ]

CAS No. :	1308298-23-8
Formula :	C₅H₄BF₃N₂O₂
M.W :	191.90
SMILES Code :	FC(C1=NC=C(B(O)O)C=N1)(F)F
MDL No. :	MFCD10696932
InChI Key :	OEZMIKKBMMAABO-UHFFFAOYSA-N
Pubchem ID :	55263556

Safety of [ 1308298-23-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 1308298-23-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.2
Num. rotatable bonds	2
Num. H-bond acceptors	7.0
Num. H-bond donors	2.0
Molar Refractivity	36.86
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	66.24 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.03
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.33
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-1.01
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.5
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.23

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.26
Solubility	10.6 mg/ml ; 0.0552 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.97
Solubility	20.4 mg/ml ; 0.106 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.43
Solubility	7.08 mg/ml ; 0.0369 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.45 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.81

Application In Synthesis of [ 1308298-23-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1308298-23-8 ]

[ 1308298-23-8 ] Synthesis Path-Downstream 1~35

1
[ 1308298-23-8 ]
[ 1401163-28-7 ]
[ 1401163-83-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; ethanol; water; at 120℃; for 0.166667h;Microwave irradiation;	Example 113(2R)-2-[({3-fluoro-6-[2-(trifluoromethyl)pyrimidin-5-yl]pyridin-2-yl}methyl)amino]-3-methylbutan-1-olA 20 mL microwave vial was charged with <strong>[1308298-23-8]2-(trifluoromethyl)pyrimidin-5-ylboronic acid</strong> (363 mg, 1.889 mmol), Example 73A (500 mg, 1.717 mmol), bis(triphenylphosphine)palladium(II) chloride (60.3 mg, 0.086 mmol), and potassium carbonate (475 mg, 3.43 mmol), followed by the addition of DME (9.0 mL), water (3.86 mL) and ethanol (2.57 mL). The mixture was heated in the microwave at 120° C. for 10 minutes. To the reaction mixture was added 100 mL 1.0 N NaOH, and extracted with 100 mL dichloromethane (2.x.). The combined dichloromethane layers were washed with 1.0 N HCl and partitioned. The resulting aqueous phase was neutralized with 3.0 N NaOH, extracted with EtOAc, and partitioned. The EtOAc layer was washed with brine, separated, dried over Na2SO4, filtered, and concentrated. The residue was purified by reverse phase chromatography. The combined fractions were concentrated. To the resulting residue was added EtOAc, and the solution was washed with 1.0 N NaOH and brine sequentially, and partitioned. The organic phase was dried over Na2SO4, filtered, and concentrated to provide the title compound as a white solid. MS (ESI+) m/z 359.0 (M+H); 1H NMR (300 MHz, DMSO-d6) delta 9.69 (s, 2H), 8.24 (dd, J=8.6, 3.7, 1H), 7.94 (dd, J=9.4, 8.7, 1H), 4.49 (t, J=5.2, 1H), 4.00 (q, J=15.0, 2H), 3.47 (dt, J=10.5, 4.7, 1H), 3.39-3.32 (m, 1H), 2.38 (dt, J=6.9, 4.7, 1H), 1.95-1.74 (m, 1H), 0.86 (t, J=7.1, 6H).

References: [1]Patent: US2012/245124,2012,A1 .Location in patent: Page/Page column 53-54.

2
[ 1308298-23-8 ]
[ 183438-24-6 ]
[ 183437-80-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 839 - 844.

3
[ 1308298-23-8 ]
[ 1049025-21-9 ]
[ 1590398-19-8 ]

Yield	Reaction Conditions	Operation in experiment
14%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 14.0h;Inert atmosphere; Sealed tube;	Example 74 2-[(4-Fluoro-benzenesulfonyl)-isopropyl-amino]-N-[2-(2-trifluoromethyl-pyrimidin-5-yl)- pyridin-4-ylmethyl] -acetamide A solution of (2-bromo-pyridin-4-ylmethyl)-carbamic acid teri-butyl ester (300 mg, 1.04 mmol), 2- (trifluoromethyl)pyrimidin-5-ylboronic acid (200 mg, 1.04 mmol) and potassium carbonate (0.14 g, 1.04 mmol) in DMF (5 mL) at 25°C was purged with nitrogen gas and evacuated three times. The solution was then treated with teira 3s(triphenylphosphine)palladium(0) (60 mg, 52 muiotaetaomicron) and then sealed and heated to 120°C for 14 h. The reaction mixture was cooled to 25°C, unsealed and poured into water. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by concentration in vacuo gave [2-(2-trifluoromethyl^yrirnidin-5-yl)-pyridin-4-ylmethyl]-carbamic acid tert-butyl ester (50 mg, 14percent) as a brown solid. M+H = 355.0.

References: [1]Patent: WO2014/49047,2014,A1 .Location in patent: Page/Page column 100; 101.

4
[ 1308298-23-8 ]
[ 1590398-20-1 ]

References: [1]Patent: WO2014/49047,2014,A1 .

5
[ 1308298-23-8 ]
[ 1590397-55-9 ]

References: [1]Patent: WO2014/49047,2014,A1 .

6
[ 1308298-23-8 ]
[ 4522-35-4 ]
[ 1621525-48-1 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; copper diacetate; caesium carbonate; In 1,4-dioxane; at 80℃;	INTERMEDIATE 57 5-(3-Iodo-lH-pyrazol-l-yl)-2-(trifluorometyl)pyrimidine A solution of 3-iodo-lH-pyrazole (0.7 g, 3.61 mmol), 2-trifluoromethylpyrimidine -4- boronic acid (0.722 g, 4.69 mmol), DMAP (1.763 g, 14.43 mmol), copper(II) acetate (0.655 g, 3.61 mmol), and cesium carbonate (2.94 g, 9.02 mmol) in 1 ,4-dioxane (18.0 mL) was heated at 80 °C overnight. The reaction was allowed to room temperature and filtered. The filtrate was diluted with EtOAc and water, and the seperated aq. layer was extracted with EtOAc. The combined organics were dried over MgS04, filtered and concentrated. The residue was purified with flash chromatography (ISCO Combiflash, 40 g, 0-5 percent EtOAc in hexanes) to give 5-(3-iodo-lH-pyrazol-l-yl)-2- (trifluorometyl)pyrimidine, as a white solid. LCMS calc. = 340.94; found = 340.88 (M+H)+. NMR (500 MHz, CDC13): 8 9.25 (s, 2 H); 7.86 (d, J= 2.5 Hz, 1 H); 6.78 (d, J= 2.7 Hz, 1 H).

References: [1]Patent: WO2014/120346,2014,A1 .Location in patent: Page/Page column 66-67.

7
5-bromo-1-oxo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester [ No CAS ]
[ 1308298-23-8 ]
tert-butyl 1-oxo-5-[2-(trifluoromethyl)pyrimidin-5-yl]-2,3-dihydro-1H-isoindole-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 120℃; for 0.5h;Microwave irradiation; Inert atmosphere;	To a microwave vial was added tert-butyl 5-bromo-1-oxo-isoindoline-2-carboxylate 2 (800 mg, 2.6 mmol), [5-(trifluoromethyl)pyrimidin-2-yl]boronic acid (584 mg, 3.1 mmol), potassium carbonate (1.1 g, 7.7 mmol), water (0.5 mL, 30 mmol) and Pd(dppf)C12 (214 mg, 0.26 mmol) in dioxane (5 mL). The reaction mixture was purged with nitrogen gas for 3 minutes and then heated to 120 °C in the microwave for 30 minutes. Upon cooling to room temperature, the resulting mixture was filtered through a thin layer of celite, washed with water and extracted with ethyl acetate. The combined organic layer was dried over Na2504, filtered and concentrated. The residue was purified by flash chromatography on silica gel, eluting with ethyl acetate /heptane (1:1) to afford the title compound 3 (700 mg, 72percent) as a white solid. LC/MS (ESI+): mlz 380.3 (M+H).

References: [1]Patent: WO2015/52264,2015,A1 .Location in patent: Paragraph 01923; 01925; 01926.

8
[ 1308298-23-8 ]
2’-(trifluoromethyl)-[4,5’-bipyrimidine]-6-carbonitrile [ No CAS ]